A superhydrophobic polyurethane-based film is described, on which the water advancing and receding contact angles are 150° and 82°, respectively. The film was prepared from surface-fluorinated polyurethane (PU), obtained from a well-defined fluorinated isocyanate, with silica particles incorporated within the film. In the absence of the silica particles, smooth fluorinated PU films with about 2 wt% fluorine demonstrate water advancing and receding contact angles of 110° and 63°, respectively. A major cause for the large contact angle hysteresis, similar to the so-called 'sticky' superhydrophobic behavior, on the roughened PU films is believed to originate from the surface reorganization of the fluorinated PU upon contact with water, which is characteristic for the partially fluorinated PU film. When a similar poly(dimethylsiloxane) (PDMS)-based roughened film was made, the water contact angle hysteresis could be reduced significantly, since the long PDMS chain can effectively suppress the surface reorganization upon contact with water.